Chimiques de thann et mulhouse



U TED STATES PATENT Orricm.

ALBERT BAUR, or GERNRODE, ASSIGNOR' TO THE FABRIQUES nus PRODUITS CH IMIQUES DE THANN- ET MULHOUSE, OF TIIANN, GERMANY.

.ARTlFlClAL M USK.

SPECIFICATION forming part of letters Patent No. 536,324, dated March 26, 1895.

Application filed NovemberBO,

To aZZ whom it may concern:

Be it known that I, ALBERT BAUR, a resident of Gernrode, in the dukedom of Anhalt, Germany, have invented certain new'and useful Improvements in the Manufacture of Artificial Musk, which are fully described in the following specification, and for which I have obtained Patents in France June 30, 1894, (certificate of addition to Patent No.195,360,)

to and in England July 4, 1894, No. 12,980.

In previous patents, Nos. 416,710, dated December 10, 1889, 451,847, dated May 5, 1891, and 481,685, dated August 30, 1892, I have describedand claimed the preparation of artificial musk by nitration of aromatic hydrocarbons containing two or three lateral chains, one of which-mustbe a butylic, amylic or propylic one, while the others are methyle or ethyle. Hydrocarbons of this family are bu- 2o tyl-toluen e, butyl-xylene and many others. I have found that not only the hydrocarbons of .the said series are able to yield musk by nitration, but ethol aromatic hydrocarbons minium, ten parts of chlorid of tertiary butyl 0 until no more evolution of hydrochloric acid takes place. I pour in water, distill the hydro; carbon with steam and purify .thebutyl-hy drindene by fractional distillation. This butyl-hydrindene is itself a new body. The boiling point of the pure hydrocarbon is 237? to 240 centigrade.

In order to transform the butyl-hydrindene into its musk-smelling trinitro derivative, it

with lateral chains for instance hydrindene 1 4:- Serial No. 580,382. (Specimens) Patented in France June 30, 1894, No. 196,360,:uu1 in England July 4, 1894, No. 12,980-

is more convenient to prepare first the dinitro compound in a state of purity and to submit it afterward to a further nitration. For this purpose I introduce ten parts of butyl: hydrindene into a well cooled mixture of'forty; parts of fuming nitric acid (specific gravity 1.48 about) and eighty parts of fuming sulfuric acid, containing about fifteen per cent. of S0,, and allow the solutionto stand a few hours. I then pour in water, filter the nitro compound, wash it with soda and afterward with water and crystallize it out of alcohol. I thus obtain white crystals melting at 121 centigrade and possessing no musky odor. I

In order to transform the dinitro into trinitro derivative I introduce ten parts of the dinitro compound into a strong nitration mixture containing forty parts of fuming nitric acid and eighty parts of fuming sulfuric acid containing from thirty to forty per cent. of S0 and heat at a temperature not exceeding 50 or 55". After a few hours I pour in water, filter and crystallize the new compound from alcohol.

The trinitrobutylhydrindene comes outin the form of white needles, sparingly soluble in cold alcohol, melting at 139 to 140 centigrade and musk odor.

I may also effect the butylation of hydrindone by introducing the same mixed with butylic alcohol in concentrated sulfuric acid. I obtain in this way a mixture of the hydrocarbon and of its sulfuric acid. The latter by nitration yields also a musk but the formerly described process is much better.

By using chlorid of propyle or anlyle instead of chlorid of butyle, I obtain derivatives 90 analogous to the butylic but presenting no advantage. It will be understood therefore that where mention is made of the butylic chlorid, the propylic and amylicchlorids are included as equivalents. It will also be im- 5 derstood that theamylic and propylio derivapossessing a very stron g Having nowparticularly described my in- I q vention and the manner in which thesaine is 0- be carried out; what I claim isli The described process of obtaining an ertificial iuskgby heating an ethoi-aromatie hydrocarbon, such 4 as hydrindene, with a chlorid such as butylie c'hlorid in presence of l a metalliechiorid, and nitrating the product 9f this reaction,

(Terivetifire bf the hydrocarbon orth. v

:5 7 2.111 the menuf ac ture of artificial musk,

the-improvement consisting in'heacing hythereby obtaining a trinitroi treated, as set drindene with butyl'ie chlerid and a metallic chlerid, thereby-producing bntyi hydrindene,

asset forth. 4 v

3. The artificial musk herein described, the

same being the trinitroderivativeof bnty1-' hydrindene in'th'eform of white needles,

sparingly soluble in alcohoi, and characterized by a strong 0301' of musk, as set forth,

In itness whereof I have hereunto signer my name in the presence-of two subscribing witnesses; r

I ALBERT BAUR.

\Vitnesses: V

'EDUARD M'i'JAzLL, .EMIL NORT. 

